Interaction of N-trimethylsilylimidazole with electrophilic trimethylsilyl compounds. Part 1. Characterisation of silylimidazolium salts

Abstract

N-Trimethylsilylimidazole forms bistrimethylsilylimidazolium salts (5) in solution with Me₃SiX (X = Br, I, OSO₂CF₃, or OCIO₃). The solutions are conducting, but evidence for ion pairing is presented. Chloro(trimethyl)silane does not produce a salt in solution at ambient temperature but does so at low temperature. N.m.r. evidence is presented for the structures, and used to obtain values of ΔH^⊖ and ΔS^⊖ for (5; X = Cl).